The best prize I've ever won... hmmm. I've won a ton of awards in school. But other than that, I won 300 dollars on a bingo game one time. I won a gameboy off a surge bottle cap. Free movies at blockbuster for a year. When I was a kid, I won so many cakes in a cake walk my family got embarassed and just gave them back. lol

I can't think of a worst prize.

My aunt has super good luck. She's won a myriad of things including a car and a years worth of gas.